The Element Effect in Nucleophilic Aromatic Photosubstitution (SN2Ar)

Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen = F, Cl, Br, I) with NaCN have been investigated. 4-Nitroanisole gave a novel, stable nitronate ion adduct (74%) with cyanide. For the five compounds, we report product distributions, Stern−Volmer kinetic plots, triplet lifetim...

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Bibliographic Details
Published in:Organic letters 2007-07, Vol.9 (15), p.2803-2806
Main Authors: Wubbels, Gene G, Johnson, Kandra M, Babcock, Travis A
Format: Article
Language:English
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Summary:Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen = F, Cl, Br, I) with NaCN have been investigated. 4-Nitroanisole gave a novel, stable nitronate ion adduct (74%) with cyanide. For the five compounds, we report product distributions, Stern−Volmer kinetic plots, triplet lifetimes, and triplet yields, which afford rate constants for attack by the cyanide ion. Cyanide attack on the fluoride is diffusion controlled; the relative rates for attack at F, Cl, Br, and I are 27:2:2:1, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070910m